CA2816093C - Compounds and compositions for the treatment of cancer - Google Patents

Compounds and compositions for the treatment of cancer Download PDF

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Publication number
CA2816093C
CA2816093C CA2816093A CA2816093A CA2816093C CA 2816093 C CA2816093 C CA 2816093C CA 2816093 A CA2816093 A CA 2816093A CA 2816093 A CA2816093 A CA 2816093A CA 2816093 C CA2816093 C CA 2816093C
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Prior art keywords
compound
cancer
anticancer agent
pharmaceutical composition
formula
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CA2816093A
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English (en)
French (fr)
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CA2816093A1 (en
Inventor
Lyne Gagnon
Lilianne Geerts
Brigitte Grouix
Pierre Laurin
Christopher Penney
Boulos Zacharie
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Liminal R&D Biosciences Inc
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Liminal R&D Biosciences Inc
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Publication of CA2816093A1 publication Critical patent/CA2816093A1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C57/32—Phenylacetic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/18—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/42—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
    • C07C57/48—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/54—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/18—Saturated compounds containing keto groups
    • C07C62/20—Saturated compounds containing keto groups with a saturated six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/04—Monocyclic monocarboxylic acids
    • C07C63/06—Benzoic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/04—Monocyclic monocarboxylic acids
    • C07C63/06—Benzoic acid
    • C07C63/08—Salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2816093A 2010-10-27 2011-10-26 Compounds and compositions for the treatment of cancer Active CA2816093C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US40706910P 2010-10-27 2010-10-27
US61/407,069 2010-10-27
PCT/CA2011/001179 WO2012097427A1 (en) 2010-10-27 2011-10-26 Compounds and compositions for the treatment of cancer

Publications (2)

Publication Number Publication Date
CA2816093A1 CA2816093A1 (en) 2012-07-26
CA2816093C true CA2816093C (en) 2020-12-01

Family

ID=46515034

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2816093A Active CA2816093C (en) 2010-10-27 2011-10-26 Compounds and compositions for the treatment of cancer

Country Status (25)

Country Link
US (2) US9114118B2 (ja)
EP (2) EP2632452B1 (ja)
JP (2) JP6007186B2 (ja)
KR (2) KR101821646B1 (ja)
CN (2) CN103347509B (ja)
AU (2) AU2011356583C1 (ja)
BR (1) BR112013010507A2 (ja)
CA (1) CA2816093C (ja)
CL (1) CL2013001152A1 (ja)
DK (2) DK2632452T3 (ja)
EA (2) EA035494B1 (ja)
ES (2) ES2703257T3 (ja)
HK (1) HK1189836A1 (ja)
IL (2) IL225599A (ja)
MX (2) MX365807B (ja)
MY (2) MY162420A (ja)
NZ (1) NZ610851A (ja)
PH (1) PH12016502324A1 (ja)
PL (2) PL3443957T3 (ja)
PT (2) PT2632452T (ja)
SG (2) SG189538A1 (ja)
TR (1) TR201819987T4 (ja)
TW (2) TWI578983B (ja)
WO (1) WO2012097427A1 (ja)
ZA (1) ZA201303035B (ja)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX365807B (es) * 2010-10-27 2019-06-14 Prometic Pharma Smt Ltd Compuestos y composiciones para el tratamiento del cáncer.
TWI689489B (zh) * 2013-03-15 2020-04-01 英商邊緣生物科技有限公司 用於治療肺纖維化、肝纖維化、皮膚纖維化及心臟纖維化之經取代之芳族化合物
RU2560702C1 (ru) * 2014-06-05 2015-08-20 Общество с ограниченной ответственностью "Научно-производственный центр "Амфион" (ООО "НПЦ "Амфион") Фармацевтическая композиция для применения в онкологии
WO2016054725A1 (en) 2014-10-10 2016-04-14 Prometic Biosciences Inc. Phenylketone carboxylate compounds and pharmaceutical compositions for the prevention and treatment of osteoporosis
SG11201702868VA (en) * 2014-10-10 2017-05-30 Prometic Pharma Smt Ltd Substituted aromatic compounds and pharmaceutical compositions for the prevention and treatment of osteoporosis
AU2015345943B2 (en) * 2014-11-12 2020-03-19 Liminal Biosciences Limited Substituted aromatic compounds and pharmaceutical compositions for tissue self-repair and regeneration
CN106267213A (zh) * 2015-05-27 2017-01-04 聊城市奥润生物医药科技有限公司 环二核苷酸cGAMP在治疗肿瘤联合用药中的应用
SG10201913998YA (en) 2017-07-25 2020-03-30 Taris Biomedical Llc Methods of treating tumor metastasis
CA3121830A1 (en) * 2018-12-05 2020-06-11 Liminal R&D Biosciences Inc. Use of sodium 2-(3-pentylphenyl)acetate in the treatment of alstrom syndrome
US11246945B2 (en) 2019-06-07 2022-02-15 National Defense Medical Center Cisplatin-loaded microbubbles, pharmaceutical composition for treatment of cancer, method for preparing pharmaceutical compositions and method for treating cancer
CN114436822B (zh) * 2022-01-12 2024-04-16 厦门稀土材料研究所 一枝蒿酮酸和生物碱复盐及其制备方法和用途

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* Cited by examiner, † Cited by third party
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EP0268907A3 (en) * 1986-11-19 1990-03-21 Carl Richard Thornfeldt Treatment of disease conditions relating to hyperactive organelles
US5605930A (en) * 1991-10-21 1997-02-25 The United States Of America As Represented By The Department Of Health And Human Services Compositions and methods for treating and preventing pathologies including cancer
ITMI20012434A1 (it) * 2001-11-20 2003-05-20 Dompe Spa Acidi 2-aril-propionici e composizioni farmaceutiche che li contengono
CN1169768C (zh) * 2002-04-26 2004-10-06 中国科学院上海有机化学研究所 （4－炔基）－芳香酮酸类化合物、合成方法及应用
AU2003303460A1 (en) * 2002-12-27 2004-07-22 Tibotec Bvba Fluorogenic enzyme substrates and methods of preparation
WO2005009104A2 (en) * 2003-07-16 2005-02-03 Ligand Pharmacueticals Incorporated Benzoic and phenyl acetic acid derivatives as hnf-4 modulators
WO2005010202A2 (en) * 2003-07-16 2005-02-03 Ligand Pharmacueticals Incorporated PHENYL ACETIC ACID DERIVATIVES AS HEPATOCYTE NUCLEAR FACTOR 4α (HNF-4α) MODULATOR COMPOUNDS
US8198328B2 (en) * 2004-01-21 2012-06-12 New York University Treatment of cancer using benzoic acid derivatives
WO2008026125A2 (en) * 2006-09-01 2008-03-06 Piramal Life Sciences Limited Anti cancer use of caffeic acid and derivatives
MX340993B (es) * 2007-02-08 2016-08-02 Emisphere Tech Inc * Agentes de suministro de acido fenilalquilcarboxilico.
MY151439A (en) * 2007-11-02 2014-05-30 Prometic Biosciences Inc Medium-chain length fatty acids and glycerides as nephroprotection agents
WO2009055932A1 (en) 2007-11-02 2009-05-07 Prometic Biosciences Inc. Substituted phenylpropionic acids as stimulators of hematopoiesis and erythropoiesis
TWI448290B (zh) * 2007-12-19 2014-08-11 Prometic Biosciences Inc 與健擇他濱（ｇｅｍｃｉｔａｂｉｎｅ）組合用於胰臟癌之治療的中等鏈長脂肪酸、鹽類及三酸甘油酯
TWI458481B (zh) 2009-05-04 2014-11-01 Prometic Biosciences Inc ３－戊基苯乙酸的鹽及其藥學用途
AU2010244930B2 (en) * 2009-05-04 2016-07-28 Liminal Biosciences Limited Substituted aromatic compounds and pharmaceutical uses thereof
MX365807B (es) * 2010-10-27 2019-06-14 Prometic Pharma Smt Ltd Compuestos y composiciones para el tratamiento del cáncer.

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ES2703257T3 (es) 2019-03-07
AU2016201556B2 (en) 2017-09-14
ZA201303035B (en) 2014-06-25
EP3443957A1 (en) 2019-02-20
KR101943280B1 (ko) 2019-01-28
JP2016188247A (ja) 2016-11-04
IL225599A (en) 2017-05-29
JP6371344B2 (ja) 2018-08-08
TW201717928A (zh) 2017-06-01
SG189538A1 (en) 2013-06-28
EP2632452A1 (en) 2013-09-04
AU2016201556A1 (en) 2016-04-14
PL3443957T3 (pl) 2021-05-04
TWI578983B (zh) 2017-04-21
EA030038B1 (ru) 2018-06-29
HK1189836A1 (zh) 2014-06-20
IL251083B (en) 2018-07-31
CL2013001152A1 (es) 2014-01-10
BR112013010507A2 (pt) 2016-08-02
CN103347509B (zh) 2016-06-08
DK3443957T3 (da) 2020-12-21
SG10201807622WA (en) 2018-10-30
EP2632452A4 (en) 2014-05-07
AU2011356583C1 (en) 2016-03-17
KR20130132448A (ko) 2013-12-04
CN105997967A (zh) 2016-10-12
MY162420A (en) 2017-06-15
CN103347509A (zh) 2013-10-09
JP2013544799A (ja) 2013-12-19
PH12016502324B1 (en) 2019-07-15
ES2837599T3 (es) 2021-06-30
MY184343A (en) 2021-04-01
JP6007186B2 (ja) 2016-10-12
WO2012097427A1 (en) 2012-07-26
PT2632452T (pt) 2019-01-10
US9439882B2 (en) 2016-09-13
NZ610851A (en) 2015-05-29
CA2816093A1 (en) 2012-07-26
TWI620563B (zh) 2018-04-11
MX2013004832A (es) 2013-05-22
IL225599A0 (en) 2013-06-27
CN105997967B (zh) 2019-08-23
IL251083A0 (en) 2017-04-30
EP3443957B1 (en) 2020-11-25
AU2011356583B2 (en) 2015-12-24
US20150313856A1 (en) 2015-11-05
EP2632452B1 (en) 2018-09-26
KR20180011332A (ko) 2018-01-31
EA201791585A1 (ru) 2018-05-31
TW201305097A (zh) 2013-02-01
TR201819987T4 (tr) 2019-01-21
EA035494B1 (ru) 2020-06-25
US9114118B2 (en) 2015-08-25
DK2632452T3 (en) 2019-01-21
PL2632452T3 (pl) 2019-03-29
MX365807B (es) 2019-06-14
PH12016502324A1 (en) 2019-07-15
EA201370103A1 (ru) 2013-12-30
MX2019007010A (es) 2019-09-06
AU2011356583A1 (en) 2013-05-09
PT3443957T (pt) 2020-12-18
KR101821646B1 (ko) 2018-01-25
US20130217645A1 (en) 2013-08-22

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